Convergent Strategy for the Pamamycin Macrodiolides: Total Synthesis of Pamamycin-607, Pamamycin-593, and Pamamycin-621D Precursors

A convergent total synthesis of pamamycin‐607 (1), isolated from Streptomyces alboniger, was achieved by an E–Z isomerization of a tetrahydrofuran alkylidene and a regio‐ and diastereoselective solvent‐dependent cyclo‐C6H11BCl/Et3N‐mediated aldol reaction as the key steps. The second key step was ex...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2007-01, Vol.46 (37), p.7086-7089
Main Authors: Lanners, Steve, Norouzi-Arasi, Hassan, Salom-Roig, Xavier J, Hanquet, Gilles
Format: Article
Language:English
Subjects:
aldol reaction
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Drug Design
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
natural products
Nuclear Magnetic Resonance, Biomolecular
Organic Chemicals - chemistry
pamamycins
regioselectivity
total synthesis
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Summary:A convergent total synthesis of pamamycin‐607 (1), isolated from Streptomyces alboniger, was achieved by an E–Z isomerization of a tetrahydrofuran alkylidene and a regio‐ and diastereoselective solvent‐dependent cyclo‐C6H11BCl/Et3N‐mediated aldol reaction as the key steps. The second key step was extended to other ketones, opening the route to new pamamycin macrodiolides, for example, pamamycin‐593 and pamamycin‐621D.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200701749